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Synthesis 1993; 1993(4): 380-386
DOI: 10.1055/s-1993-25868
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Procedures for the Selective Alkylation of Calix[6]arenes at the Lower Rim

Rob G. Janssen* , Willem Verboom, David N. Reinhoudt, Alessandro Casnati, Margret Freriks, Andrea Pochini, Franco Ugozzoli, Rocco Ungaro, Pedro M. Nieto, Mar Carramolino, Félix Cuevas, Pilar Prados, Javier de Mendoza
  • *Laboratory of Organic Chemistry, University of Twente, NL-7500 AE Enschede, The Netherlands
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Publication History

Publication Date:
17 September 2002 (online)

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New partially alkylated calix[6]arenes have been synthesized. Depending on the conditions, mono-, 1,2-di-, 1,3-di, 1,2,3-tri-, 1,3,5-tri-, 1,2,4,5-tetra-, and 1,2,3,4,5-pentamethylated derivatives of p-tert-butylcalix[6]arene could be obtained in moderate to good yields. Methylation or benzylation of the parent calix[6]arene showed a regioselectivity towards 1,2-di-, and 1,2,3-trisubstitution. The solid state structure of 1,2,4,5-tetrasubstituted p-tert-butylcalix[6]arene [R=O(CH2CH2O)2CH3] has been elucidated by X-ray analysis.